Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes.
Org Lett. 2003 Jun 26; 5(13):2303-6.OL

Abstract

A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield. [reaction: see text]

Authors+Show Affiliations

Denmark SE

Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, USA. denamrk@scs.uiuc.edu

Heemstra JR

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12816434

Citation

Denmark, Scott E., and John R. Heemstra. "Lewis Base Activation of Lewis Acids. Catalytic Enantioselective Addition of Silyl Enol Ethers of Achiral Methyl Ketones to Aldehydes." Organic Letters, vol. 5, no. 13, 2003, pp. 2303-6.

Denmark SE, Heemstra JR. Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes. Org Lett. 2003;5(13):2303-6.

Denmark, S. E., & Heemstra, J. R. (2003). Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes. Organic Letters, 5(13), 2303-6.

Denmark SE, Heemstra JR. Lewis Base Activation of Lewis Acids. Catalytic Enantioselective Addition of Silyl Enol Ethers of Achiral Methyl Ketones to Aldehydes. Org Lett. 2003 Jun 26;5(13):2303-6. PubMed PMID: 12816434.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes. AU - Denmark,Scott E, AU - Heemstra,John R,Jr PY - 2003/6/21/pubmed PY - 2003/6/21/medline PY - 2003/6/21/entrez SP - 2303 EP - 6 JF - Organic letters JO - Org Lett VL - 5 IS - 13 N2 - A highly enantioselective addition of silyl enol ethers derived from simple methyl ketones is described. The catalyst system of silicon tetrachloride activated by a chiral bisphosphoramide (R,R)-7 effectively promotes the addition of a variety of unsubstituted silyl enol ethers to aromatic, olefinic, and heteroaromatic aldehydes in excellent yield. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12816434/Lewis_base_activation_of_Lewis_acids__Catalytic_enantioselective_addition_of_silyl_enol_ethers_of_achiral_methyl_ketones_to_aldehydes_ DB - PRIME DP - Unbound Medicine ER -

Tags

Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes.Org Lett. 2003 Jun 26; 5(13):2303-6.OL